Triethylamine → 4,7-Diazaspiro[2.5]octane-4-carboxylic acid, 7-(3-oxetanyl)-, phenylmethyl ester

HRID 1922714Notes

Reaction equation

HRID 1922714 reaction equation
C(O)(=O)C(O)=O.[CH2:7]([O:14][C:15]([N:17]1[CH2:24][CH2:23][NH:22][CH2:21][C:18]21[CH2:20][CH2:19]2)=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[O:25]1[CH2:28][C:27](=O)[CH2:26]1.CCN(CC)CC.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:7]([O:14][C:15]([N:17]1[CH2:24][CH2:23][N:22]([CH:27]2[CH2:28][O:25][CH2:26]2)[CH2:21][C:18]21[CH2:20][CH2:19]2)=[O:16])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 150242543-OxetanoneHCID 674922174,7-Diaza-spiro[2.5]octane-4-carboxylic acid benzyl ester oxalate

Product 1

HCID 596059144,7-Diazaspiro[2.5]octane-4-carboxylic acid, 7-(3-oxetanyl)-, phenylmethyl ester

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 4,7-diazaspiro[2.5]octane-4-carboxylic acid benzyl ester oxalate (200 mg, 0.59 mmol), oxetan-3-one (50 mg, 0.69 mmol), NEt3 (82 μL, 0.59 mmol) and 4 Å powdered molecular sieves (1.0 g) in DCE (10 mL) was stirred at r.t. for 2 h before the addition of sodium triacetoxyborohydride (164 mg, 0.78 mmol). The resulting mixture was stirred for 68 h then loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH and the product eluted with 2M NH3/MeOH affording the title compound. LCMS (method H): RT 2.01 min, [M+H]+ 303.3

Workup

  1. washwas washed with MeOH
  2. washthe product eluted with 2M NH3/MeOH affording the title compound
  3. customRT 2.01 min, [M+H]+ 303.3

Sources & evidence

ORD record
ord-a3b36fb091a34d31998200b30a0554ab
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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